Trifluoroacetic acid → HCID 88157772, compound

HRID 992715Notes

Reaction equation

HRID 992715 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:69]/[O:70][CH3:71])/[C:15]([NH:17][C@@H:18]2[C:67](=[O:68])[N:20]3[C:21]([C:51]([O:53]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:52])=[C:22]([S:25][CH2:26][C:27]4[CH:28]=[N:29][N:30](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:31]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1>C1(OC)C=CC=CC=1.ClCCl>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:69]/[O:70][CH3:71])/[C:15]([NH:17][C@@H:18]2[C:67](=[O:68])[N:20]3[C:21]([C:51]([OH:53])=[O:52])=[C:22]([S:25][CH2:26][C:27]4[CH:28]=[N:29][NH:30][CH:31]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 88158028HCID 88158028, compound

Product 1

HCID 88157772HCID 88157772, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Under nitrogen atomosphere, 1 ml of trifluoroacetic acid was added slowly to a solution of 500 mg of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate in anisole (0.5 ml) and dichloromethane (1.5 ml) at 0° C. The mixture was warmed to a room temperature and stirred for 2 hours. The mixture was poured into IPE and the resulting precipitate was collected by filtration. The precipitate was dissolved in pH 6.86 buffer and chromatographed on a HP-20 (eluent: water-methanol). The eluate was lyophilized to afford 171.6 mg of 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid.

Workup

  1. additionThe mixture was poured into IPE
  2. filtrationthe resulting precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in pH 6.86 buffer
  4. customchromatographed on a HP-20 (eluent: water-methanol)

Sources & evidence

ORD record
ord-ef2437235cf34448bc2e4b9922054e6c
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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